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This thesis explores high-end and bespoke menswear, tailoring and fashion, asking the question - why do some men choose to spend large sums of money to have clothes made for them? Using tailors and high-end menswear as a lens, this thesis unpacks how men construct their notion of self in the digital and terrestrial worlds through the clothes that they wear and the identities they perform. Based on twelve months' terrestrial fieldwork in London and twenty-four months' concurrent digital fieldwork with Instagram, this thesis examines notions of dress, performance and the individual across a multi-dimensional fieldsite set within a blended digital and terrestrial landscape. The fieldwork comprised visiting and interviewing tailors, and observing inside their workshops and at their fashion shows. In addition, the analyst-as-client built relationships with tailors, and constructed a digital self within Instagram through the publication of self-portraits and images of clothing. This thesis is presented in four chapters, flanked by an Introduction and Conclusion. These chapters move from an exploration of terrestrial research in the first two, to an analysis of digital research in the latter two. Five major motifs emerge in this thesis: the importance of the anthropology of clothing and adornment within western society; the nature of the individual in a digitised world; the difficulty in conducting western-centric fieldwork without an element of digital analysis; a methodological restructuring of digital anthropology; and the idea that a digital self can acquire agency. This thesis employs a pioneering blended methodology which brings together the fields of digital anthropology, visual anthropology and material culture to question how selves are constructed in a rapidly changing and increasingly digitised modernity. In conclusion, the thesis argues that individuals construct multiple digital selves and a sense of identity (around the notion of 'authentic individualism') that is illusory.